Sodium Methoxide → 6-Hydroxy-2a-[4-(2-methoxyphenylpiperazinyl)butyl]-2a,3,4.5-tetrahydrobenz[cd]indole-2(1H)-one

HRID 276915Notes

Reaction equation

HRID 276915 reaction equation
C([O:4][C:5]1[CH:13]=[CH:12][C:11]2[NH:10][C:9](=[O:14])[C:8]3([CH2:18][CH2:19][CH2:20][CH2:21][N:22]4[CH2:27][CH2:26][NH:25][CH2:24][CH:23]4[C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[O:34][CH3:35])[CH2:15][CH2:16][CH2:17][C:6]=1[C:7]=23)(=O)C.C[O-].[Na+]>CO>[OH:4][C:5]1[CH:13]=[CH:12][C:11]2[NH:10][C:9](=[O:14])[C:8]3([CH2:18][CH2:19][CH2:20][CH2:21][N:22]4[CH2:27][CH2:26][NH:25][CH2:24][CH:23]4[C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[O:34][CH3:35])[CH2:15][CH2:16][CH2:17][C:6]=1[C:7]=23

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 226295506-Acetoxy-2a-[4-(2-methoxyphenylpiperazinyl)butyl]-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one

Product 1

HCID 226295726-Hydroxy-2a-[4-(2-methoxyphenylpiperazinyl)butyl]-2a,3,4.5-tetrahydrobenz[cd]indole-2(1H)-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A methanol solution of 121 mg (0.25 mmol) of 6-acetoxy-2a-[4-(2-methoxyphenylpiperazinyl)butyl]-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H) -one was mixed with 30 mg of methanol solution of sodium methoxide and the mixture was stirred at a room temperature for 3 hours. By evaporating the solvent under a reduced pressure and recrystallizing the resulting residue from chloroform-ethyl acetate, the title compound was obtained quantitatively.

Workup

  1. customBy evaporating the solvent under a reduced pressure
  2. customrecrystallizing the resulting residue from chloroform-ethyl acetate

Sources & evidence

ORD record
ord-cf6491e5037148748233d26a2d0b1dc4
Source dataset
uspto-grants-2002_03
Patent number
US06355642B1

Reaction notes

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